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【结 构 式】

【分子编号】48820

【品名】2,4-Dihydroxybenzenecarboxylic acid; 2,4-Dihydroxybenzoic acid; beta-Resorcylic acid; Resorcinol-4-carboxylic acid

【CA登记号】89-86-1

【 分 子 式 】C7H6O4

【 分 子 量 】154.12224

【元素组成】C 54.55% H 3.92% O 41.52%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

The reaction of 3,5-dihydroxybenzoic acid (I) with N,O-dimethylhydroxylamine (II) by means of EDC and NMM in dichloromethane gives the N,O-dimethylbenzamide (III), which is alkylated with butyl bromide (IV) and K2CO3 in hot DMF to yield the dibutoxybenzamide (V). The condensation of (V) with 4-methylpyridine (VI) by means of LDA in THF affords 1-(2,4-dibutoxyphenyl)-2-(4-pyridyl)ethanone (VII), which is oxidized with SeO2 in hot acetic acid to provide the dione (VIII). Finally, this compound is cyclized with 4-chlorobenzaldehyde (IX) and ammonium acetate in refluxing acetic acid to furnish the target imidazole.

1 Chang, L.L.; et al.; Substituted imidazoles as gluagon receptor antagonists. Bioorg Med Chem Lett 2001, 11, 18, 2549.
2 de Laszlo, S.; O'Keefe, S.; Li, B.; MacCoss, M.; Rolando, A.; mantlo, N.; Koch, G.; Cascieri, M.A.; Hagmann, W.K.; Chang, L.L.; Pang, M.; Sidler, K.L.; Selective, non-peptide antagonists for the glucagon receptor: Substituted imidazoles. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 237.
3 Chang, L.L. (Merck & Co., Inc.); Triaryl substd. imidazoles as glucagon antagonists. EP 0959886; JP 2000514088; US 5880139; WO 9822109 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 48820 2,4-Dihydroxybenzenecarboxylic acid; 2,4-Dihydroxybenzoic acid; beta-Resorcylic acid; Resorcinol-4-carboxylic acid 89-86-1 C7H6O4 详情 详情
(II) 13361 (Methoxyamino)methane; N,O-Dimethylhydroxylamine 1117-97-1 C2H7NO 详情 详情
(III) 48821 2,4-dihydroxy-N-methoxy-N-methylbenzamide C9H11NO4 详情 详情
(IV) 28721 1-bromobutane 109-65-9 C4H9Br 详情 详情
(V) 48822 2,4-dibutoxy-N-methoxy-N-methylbenzamide C17H27NO4 详情 详情
(VI) 31150 4-methylpyridine 108-89-4 C6H7N 详情 详情
(VII) 48823 1-(2,4-dibutoxyphenyl)-2-(4-pyridinyl)-1-ethanone C21H27NO3 详情 详情
(VIII) 48824 1-(2,4-dibutoxyphenyl)-2-(4-pyridinyl)-1,2-ethanedione C21H25NO4 详情 详情
(IX) 29029 4-chlorobenzaldehyde 104-88-1 C7H5ClO 详情 详情
Extended Information